Monoazodyestuffs



wherein-one m stands for an acldyl amino Patented Dec. 15, 15133].

UNITED STATES P-ATENT OFFKIE ILHELM EELMEIER ANQD EUGEN GLIETENBERG, 0F LE-VERKUsEN-oN-THE-RHINE,

GERMANY, Assronons T0 GENERAL ANILINE WORKS, mo, OF NEW YORK, N. Y, A

CORPORATION 01* DELAWARE MONO-AJZODYESTUFFS N'o Drawing. Applicationliled March 1, 1929. Serial No. 343,842, and in Germany March 2, 1928.

The present invention"relates to monoazodyestufi's, more particularly, it relatesto dyestufl's of the general formula:

group, such as -NH CQCH NHCO CfiHr the others stands for an alkoxy-, aralkoxy-, ar yloXyor a methyl-group, and 3 stands for an alkoXy-, aralkoxy, aryloxyor a methyl-group, but only one of the symbols a: and 3 being a methyhgroup, ac stands for, an acidyl-group, and n stands for one of the numbers 1 and2.

Our new compounds are obtainable by diazotizing in the usual manner with sodium nitrite and hydrochloric. acid an amine of the general formula h g (il 1'8 m fo' flan acidyLat-nino map, the other lstand'sfor'anfalkoxy alkoxya 3 or ameth'yl-gr'oup, and 2/ wherein adstands for an acidyl group, for ozrample for an acctylor benzoyl-group, and it. stands for one of the numbers 1 and 2, While stirring; when the coupling is complete, the dyestufi' is isolated in the usual manner.

The new dyestufi's are in the dry pulyerized form dark, various colored powders, which are soluble in water, and'whiohjfiye wool from an acid bath clear reddish violet to greenish blue shades. 4 The dyeing's are distinguished by their evenness and fastness to alkalies and acids, besides they are iast to light, washing and hot-pressing. f l The invention is illustrated by the following examples, but is not restricted thereto;

Ewample 1.21 0 parts by Wei ht of fi-acet amino-Q-amino 1.4 dimethoxy e nzene' are dissolved in water with the addition ofthydrochloric acid and diazotized with sodium nitrite in the usual manner. The diazo soluw 1 tion is slowly introduced into a solution of 405 parts by weight of the-sodium5salt of 1-acetamino-8 hydroxy naphthalene --3. 5-di sulfonic acid in aqueous pyridine. The coupling is complete in a short time. The solu-;

tion of the dyestufi is diluted with water, and I the dyestufl is salted out and-filtered. In the free state the dyestuff has probably the following formula:

CHI If instead of pyridine,soda or sodium bicarbonate is used in the coupling process, the coupling proceeds somewhat more slowly.

The new dyestuffdyes wool from an acid bath clear even reddish-blue shades of good fastness to carbonization, light, washing and hot-pressing. c

If in the above example the acetyl residue of the l-acetylamino-8-hydroxy-naphthalene-v 3.6-disulfonic acid is replaced by a car: bethoXy-(COOCJ-L), chloro-acetyl-, ,B-chloro-propionyL, phenylacctylor a substituted or unsubstituted benzoyl-residue, dyestuffs of the same properties, dyeing wool more red or more blue, according to thespecific acidylresidue used, are obtained.

Ewarmplc 2.-A diaz o solution prepared in the usual manner from 210 parts hy'weight of (i-an'iino-l-acetylamino-l.S-dimethoXy-benzene are introduced into a soda alkaline solution of 361 parts by weight of l-acetainino 8-hydroxy-naphthalene-3.6-disulfonic acid. 5 whenthecouplingis finished the dyestufl is saltedou-u'filtered: and dried? lhe new dyestufi' dyes wool from an acid bath powerful even clear violet shadesof good fastncss to carbonization, light, Washing and hotpressing. i

If the acctyl-residue of the 6-an1ino-4- acctaniino-LS-dimethoxybenzene is replaced by any other acidyhresiduc, for example, by a benzoiylr, a fi-ohloro ei'hane-sulfo-,a toluenesulfoor similar residues, dyestuffs of the same fastnessprope'rties, dyeing wool inore red'er inore blua'varyingg; tvith the specific acidyl-residues used, are obtained. *Ewample parts-by Weight of lmethox-y fi acetamino 2 arnino -1 methylbenzene are dissolved and dia'zptized irrthe usual nianneri 'The diaze 'solnt-ion-is slowly introduced While *stipring' inte agenda alkaline solutionof 1361 partsby weight of l-acetaniinog8-hydroxynaphthalene 3.6 disulfonic acid. When the diazo compound can no more be, detected, the dyestuff is isolated in the usual manner. It dyes Woolirom an acid bath in very clear even reddish violet shades, so of good fastness to carbonization, light, Wash ing andhot-pressingu'fl i If the acetyl resid ue s" of the two components are replaced by ai'iy ot-her acidyl residue, dyestuffs of the same f'asthess properties are obtained. Y

E trample J-The diazo "compound pre- -pared'fron1 272 parts by Weight of 5 aniino- 4- phenOXy- Q. acetylamino 1 niethoxy-benzeno are coupled with an aqueous solution of 361 pantsbyimei'ght of l-aoetannino-8-hydroxynaphthalenee3.6;disulfonic acid in the presence of pyridine or soda; The new dyestuff is isolated in the usualmanner, it dyes wool from an acid-bath clear bluish violet shades of good fastness to carbonization, light, wash ing and hot pressing, V

If the phenoXy-residue'of the diazotizing component is substituted by V a benzyl-hy- ,droXy-residue, a dyestufi is obtained, dyeingwool more blue. If the diazo cornpound prepared from 5-amino 4=-phenoxy-2-acetylamino-l-methoxybenzene is coupled in an alkaline medium with l- (B-chloroethanesulfo) amino-S-hydroxylmphthalene 3.6 disulfonic acid, a dyestuflf, dyeing reddish-bluc shades, is obtained. By coupling of 1-(4-,toluenesulfo) -aniino-8- hydroxynaphthalenc 3.6 disulfonic acid with the diazo compound from 5-aininol ethoxy-2-acetylamino -lrnethoxybenzene a dyestufl, dyeing WOOl similar shades is obtained; its solubility can be increased by substituting the l- (r lwtoluenesulfo) amino- Sl-hydroxynaphtlialcne-3.6-disulfonic acid by $55 the l-(5-acetylaIni110-2-n1cthylbenzenesuli (so all) n wherein one a! stands for an acidylarnino group, the, other wstands for a substituent of the group consistinv ofthe alkoxy-, aralkoxy, :iryloxye and methyl-groups, y stands for a suhsti-tuent of the; groups-consisting of he all oXy-, arulkoxy, anyloxy-, :and: methylgroups, but only one of the symbols m and 3 being a methyl-group, ac stands for an .85 aoidyl residue, and n stands for one of the numbers 1 and 2, being in thedry ulverized form dark, various colored powdtrs, soluble in Water and dyeing Wool from an acid bath even clear reddish violet to greenishblue shades of good fastness to alkalies, acids, light, Washing and hot-pressing.

2. As new products monoazo dyestufis of the probable general formula:

' v on NHac wherein one stands for an acidylamino group, the other a and y stand for alkoxygroups and ac stands for an acidyl residue, being in the dry pulverized form dark, various colorecL powders, soluble in Water and dyeing wool from an acid bath even clear reddish violet to greenish blue shades of good fastness to alkalies, acids, light, washing and hohpressing.

4. As new products monoazo dyestuifs of the probable general formula:

(SOuHh HaU-C O-BN HOxS SO|H dyeing WOOl from an acid bath clear even reddish-blue shades of good fastness to carbonization, light, Washing and hot-pressing.

In testimony whereof we have hereunto set our hands.

WILHELM NEELMEIER. [L. 8.] EUGEN GLIETENBERG. [L. 3.]

4. As new products monoezo dyestufls of the probable general formula:

a CH NH-oc HaU-O 0-HN H015 80:1! 25 dyeing wool from an acid bath clear even reddish-blue shades of good fastness to carbonization, light, washing and hot-pressing. In testimony whereof We have hereunto set our hands.

WILHELM NEELMEIER. [11. s.] EUGEN GLIETENBERG. [Le] CERTIFICATE OF CORRECTION.

Potent No. 1,836,182. Granted December 15, 1931, m

WILHELM NEELMEIER ET AL.

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 1, line 68, for "naphthalene-354i read naphthalene-3.6-di-; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office.

Signed and sealed this 29th day of March, A. D. 1932.

M. J. Moore, (Seal) Acting Commissioner of Patents.

CERTIFICATE OF CORRECTION.

Patent No. 1,836,182. Granted December 15, 1931, to

WILHELM NEELMEIER ET AL.

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 1, line 68, for "naphthaIenc-3.5-di-" read naphthalene-3.6-di-; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office.

Signed and sealed this 29th day of March, A. D. 1932.

M. J. Moore,

(Seal) Acting Commissioner of Patents. 

